12 Night - Southern Caribbean Holiday & Aruba, Bonaire & Curacao
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Terre-de-Haut, Iles des Saintes, Guadeloupe, Carambola Beach, Saint Kitts and Nevis, Little Bay, Montserrat, Willemstad AN, Curacao, Oranjestad, Aruba, Kralendijk, Bonaire, Saint Georges, Grenada, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados
2025 Sails: Dec 22, More...

7 Night - Windward Islands
Starting in Bridgetown, Barbados, Rodney Bay, St Lucia, Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
2025 Sails: Dec 27, 2026: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, More...

14 Night - Yachtsman's Island Jewels
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Saint Pierre, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Pointe-a-Pitre, Guadeloupe, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Jan 31, More...

10 Night - Cruise Roundtrip from Bridgetown
Starting in Bridgetown, Barbados, Rodney Bay, South Friars Bay, Philipsburg, Gustavia, Terre De Haut, Iles des Saintes, Mayreau, Tobago Cays, Port Elizabeth VC, Bequia, Bridgetown, Barbados
2026 Sails: Feb 1, More...

14 Night - Yachtsman's Island Jewels
Starting in Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Pointe-a-Pitre, Guadeloupe, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Feb 7, More...

7 Night - Caribbean Gems
Starting in Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Pointe-a-Pitre, Guadeloupe, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Feb 7, More...

11 Night - Barbados & Caribbean Gems Cruise
Starting in Bridgetown, Barbados, Rodney Bay, Portsmouth UK, Gustavia, Philipsburg, South Friars Bay, Terre De Haut, Iles des Saintes, Tobago Cays, Port Elizabeth VC, Bequia, Mayreau, Bridgetown, Barbados
2026 Sails: Feb 11, More...

11 Night - Fort Lauderdale to Bridgetown
Starting in Fort Lauderdale, Florida, San Juan, St John VI, Gustavia, St Barthelemy, Philipsburg, St Maarten, Deshaies, Fort-de-France, Rodney Bay, Bequia, Bridgetown
2026 Sails: Feb 12, More...

7 Night - Windward Islands Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Rodney Bay, Le Marin, Terre De Haut, Iles des Saintes, Falmouth Bay, Philipsburg
2026 Sails: Feb 22, More...

14 Night - Yachtsman's Island Jewels
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Saint Pierre, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Pointe-a-Pitre, Guadeloupe, Trois Ilets, Martinique, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Mar 7, More...